Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols.
The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-L-chiro-inositol and deoxythiocyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihydroxylations, and the results were studied regarding reaction conditions and co-catalyst for different derivatives. The new compounds were included in a minilibrary of deoxygenated cyclitols and evaluated for their capacity to influence the feeding behavior of Epilachna paenulata (Coleoptera: Coccinellidae), a common pest of the Curcubitaceae crops.
Bellomo
Ana
A
Laboratorio de Síntesis Orgánica, D.Q.O, Fac. de Química, Univ. de la República, C.C. 1157 Montevideo, Uruguay.
Camarano
Soledad
S
Rossini
Carmen
C
Gonzalez
David
D
D000818:Animals; D001517:Coleoptera; D054812:Cyclitols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005247:Feeding Behavior / Q000187:drug effects; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry*
D054812:Cyclitols; D013455:Sulfur